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ACTIVE PHARMA INGREDIENTS

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Chemistry

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Also known as: 1h-indole, 120-72-9, 2,3-benzopyrrole, Indol, 1-benzazole, Ketole

Molecular Formula

C₈H₇N

Molecular Weight

117.15 g/mol

InChI Key

SIKJAQJRHWYJAI-UHFFFAOYSA-N

FDA UNII

8724FJW4M5

indole is a natural product found in Tetrastigma hemsleyanum, Lonicera japonica, and other organisms with data available.

1 2D Structure

Indole

2 Identification

2.1 Computed Descriptors

2.1.1 IUPAC Name

1H-indole

2.1.2 InChI

InChI=1S/C8H7N/c1-2-4-8-7(3-1)5-6-9-8/h1-6,9H

2.1.3 InChI Key

SIKJAQJRHWYJAI-UHFFFAOYSA-N

2.1.4 Canonical SMILES

C1=CC=C2C(=C1)C=CN2

2.2 Other Identifiers

2.2.1 UNII

8724FJW4M5

2.3 Synonyms

2.3.1 MeSH Synonyms

1. Indole Hydrochloride

2. Indole, 14c-labeled

2.3.2 Depositor-Supplied Synonyms

1. 1h-indole

2. 120-72-9

3. 2,3-benzopyrrole

4. Indol

5. 1-benzazole

6. Ketole

7. 1-azaindene

8. Benzopyrrole

9. 2,3-benzopyrole

10. Caswell No. 498b

11. Indol [german]

12. Indole (natural)

13. 1-benzo(b)pyrrole

14. 1h-benzo[b]pyrrole

15. Fema No. 2593

16. Ccris 4421

17. Hsdb 599

18. Epa Pesticide Chemical Code 025000

19. Benzo[b]pyrrole

20. Ai3-01540

21. 1h-indole, Homopolymer

22. Mfcd00005607

23. Chembl15844

24. Chebi:16881

25. 8724fjw4m5

26. Nsc-1964

27. Indole 100 Microg/ml In Acetonitrile

28. Ncgc00167539-01

29. Dsstox_cid_737

30. Dsstox_rid_75761

31. Dsstox_gsid_20737

32. 82451-55-6

33. Ind

34. Cas-120-72-9

35. Nsc 1964

36. Einecs 204-420-7

37. Benzazole

38. Mono-indole

39. Unii-8724fjw4m5

40. 1-h-indole

41. Indole, 7

42. Indolum

43. Indole (8ci)

44. Indole (white Flake)

45. Indole, 98%

46. 1h-indole (9ci)

47. Indolum [hpus]

48. Indole [fhfi]

49. Indole [hsdb]

50. Indole [fcc]

51. Indole [usp-rs]

52. Indole [mi]

53. Indole, >=99%

54. Schembl698

55. Bmse000097

56. Indole, Analytical Standard

57. Indole, >=99%, Fg

58. Wln: T56 Bmj

59. Bidd:gt0304

60. Schembl940818

61. Indole Benzo-pyrrole

62. Schembl1921769

63. Schembl9559244

64. Dtxsid0020737

65. Amy3411

66. Nsc1964

67. 185l

68. Bcp27232

69. Str01201

70. Tox21_112536

71. Tox21_201677

72. Tox21_302937

73. Bbl011739

74. Bdbm50094702

75. S6358

76. Stl163380

77. Zinc14516984

78. Akos000119629

79. Tox21_112536_1

80. Cg-0501

81. Cs-w001132

82. Db04532

83. Hy-w001132

84. Indole, Puriss., >=98.5% (gc)

85. Ncgc00167539-02

86. Ncgc00167539-03

87. Ncgc00256348-01

88. Ncgc00259226-01

89. Bp-10563

90. Ds-011308

91. Ft-0627211

92. I0021

93. C00463

94. I-0800

95. I-0810

96. Q319541

97. Sr-01000944736

98. Sr-01000944736-1

99. Z57833933

100. F2190-0647

2.4 Create Date

2004-09-16

3 Chemical and Physical Properties

Molecular Formula	C₈H₇N
Molecular Weight	117.15 g/mol
XLogP3	2.1
Hydrogen Bond Donor Count	1
Hydrogen Bond Acceptor Count	0
Rotatable Bond Count	0
Exact Mass	117.057849228 g/mol
Monoisotopic Mass	117.057849228 g/mol
Topological Polar Surface Area	15.8 Å²
Heavy Atom Count	9
Formal Charge	0
Complexity	101
Isotope Atom Count	0
Defined Atom Stereocenter Count	0
Undefined Atom Stereocenter Count	0
Defined Bond Stereocenter Count	0
Undefined Bond Stereocenter Count	0
Covalently Bonded Unit Count	1

4 Pharmacology and Biochemistry

4.1 Metabolism/Metabolites

INDOLE UNDERGOES SCISSION OF PYRROLE RING TO YIELD N-FORMYLANTHRANILIC ACID, AN UNSTABLE COMPD WHICH DECOMP INTO ANTHRANILIC ACID & FORMIC ACID. INDOLE IS FIRST HYDROXYLATED TO GIVE INDOXYL & THEN ISATIN, & IT IS PROBABLY LATTER WHICH UNDERGOES HYDROLYTIC RING OPENING.

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 69

...INDOLE IS METABOLIZED BY RAT TO INDOXYL, OXINDOLE, 5-HYDROXYOXINDOLE & ISATIN...

Parke, D. V. The Biochemistry of Foreign Compounds. Oxford: Pergamon Press, 1968., p. 45

YIELDS 2,2-BIS(3-INDOLYL)INDOXYL IN HORSERADISH. DEOXYVIOLACEIN IN CHROMOBACTERIUM. CIS-6,7-DIHYDRO-6,7-DIHYDROXYINDOLE PROBABLY IN PSEUDOMONAS. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. I-2

YIELDS 3,3'-DIINDOLYLACETIC ACID IN PEA. O-FORMAMIDOBENZALDEHYDE IN TECOMA. 3-HYDROXYOXINDOLE IN COCCUS. /FROM TABLE/

Goodwin, B.L. Handbook of Intermediary Metabolism of Aromatic Compounds. New York: Wiley, 1976., p. I-3

For more Metabolism/Metabolites (Complete) data for INDOLE (10 total), please visit the HSDB record page.

Indole has known human metabolites that include 6-Hydroxyindole, Indoxyl, and Oxindole.

S73 | METXBIODB | Metabolite Reaction Database from BioTransformer | DOI:10.5281/zenodo.4056560

4.2 Mechanism of Action

The effects of heterocyclic cmpd on hepatic xenobiotic metabolizing enzymes were studied in mice. Female CD-1 mice were admin 5 u mol/kg coumarin, trimethylene oxide (TMO), or trimethylene sulfide (TMS) for 6 days by gavage, or benzofuran, indole, or indole-3-carbinol (IC) daily for 10 days. Animals were /sacrificed/ 1 or 2 days after the last dose; livers were removed and assayed for epoxide hydrolase, glutathione-S-transferase (GST), reduced NADH-quinone-reductase (NADH/QR), glucose-6-phosphate-dehydrogenase (G6PDH), glutathione-reductase (GSSG-red), uridine-diphosphate-glucose-dehydrogenase (UDPGDH), aniline-hydroxylase, 7-ethoxycoumarin-deethylase (ECOD), and cytochrome-c-reductase (cyt-c-red) activities, and cytochrome p450. All cmpd except indole, significantly enhanced epoxide hydrolase activity. GST activities were elevated by all cmpd except TMO and TMS. NADH/QR activity was incr only by coumarin and benzofuran. Indole incr only GST, UDPGDH and cyt-c-red activities. IC enhanced GST, UDPGDH, cyt-c-red, epoxide hydrolase and cytochrome p450 and related monooxygenase activities. Benzofuran and coumarin showed more varied responses. Both cmpd incr epoxide hydrolase, GST and NADH/QR activities. Benzofuran decr cytochrome p450 content and elevated ECOD activity.

Heine HS et al; Chemico-Biol Interact 59 (2): 219-30 (1986)

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